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Tactical Wealth is the podcast built to empower the military and veteran community to take control of their financial future.
From navigating the military to civilian life transition, to launching businesses, growing your income, and building long-term wealth, each episode brings you real stories and actionable insights from those who’ve gone from boots on the ground to building lasting wealth.
Hosted by Kaj Larsen, former Navy SEAL, award-winning journalist, and mission-driven entrepreneur. Kaj successfully co-founded a financial technology company and sold the company in 2024. The podcast features hard truth conversations with successful veteran entrepreneurs, CEOs, and top financial experts.
Whether you're still in uniform or already charting your next chapter, this podcast gives you the tactical tools to lead with impact in your finances and beyond. Let’s get tactical.
Tactical Wealth is a Gebbia Media production, brought to you by Siebert.Valor, a military-focused initiative from Siebert Financial. The Tactical Wealth podcast is for informational and entertainment purposes only. The views expressed by guests are their own and do not necessarily reflect those of Siebert Financial. This podcast does not constitute investment advice, an offer to sell, or a solicitation to buy any securities. Past performance is not indicative of future results. Listeners should consult a qualified financial professional before making any investment decisions.
For more information and disclosures, please visit siebert.com/disclosures.
00;00;04;10 - 00;00;21;07
Unknown
A lot of times people think when they need to start a company, they need to go out and do it in their garage. And sometimes it makes a lot more sense to do it when you have some infrastructure and support around you, and it can take away some of the risk. We just saw that there was magic there, people were getting better and that PTSD was something that people could recover from.
00;00;21;07 - 00;00;37;13
Unknown
But I think we come from a culture where people don't want to fail. And I think you also have to recognize that there's going to be times when you fail, and that's totally fine, and sometimes an early failure that redirects you. It's totally fine. Being quizzed of be humble, make sure you're taking care of your people and that you care about them and that you're putting them.
00;00;37;14 - 00;00;56;11
Unknown
You're making sure they're working on problems that are really important.
00;00;56;13 - 00;01;18;18
Unknown
Some people wait for others. Fight for it. Welcome to Tactical Wealth, the show. We're disciplined service and real world experience become pathways to financial power. I'm your host Kaj Larsen. On each episode, we bring you the stories and the wisdom of those who have gone from boots on the ground to successful careers for military to wealth and how they've done it.
00;01;18;18 - 00;01;28;28
Unknown
So you can apply those insights to your own mission and your own life. This is tactical wealth, from military to money.
00;01;29;00 - 00;01;53;03
Unknown
Welcome back to another episode of Tactical Wealth. We're here from our forward deployed location in the heart of Brooklyn, which would make my dad proud. He's a proud Brooklynite. And today's guest, I think my producer, Angie, would tell you I have been unduly excited about talking to. He is a marine Corps veteran. He's an entrepreneur, he is a public servant, and he's also my friend.
00;01;53;03 - 00;02;15;10
Unknown
I'm proud to call him my friend, and I'm proud of the work that he's done for our country. Zach Iscol fought in the Battle of Fallujah. He went on to found a media company dedicated to the military community. He was also the founder of the Headstrong Project, which I don't think I've ever talked about this publicly. I was a beneficiary.
00;02;15;13 - 00;02;37;00
Unknown
Yeah, yeah, yeah, yeah. You see, you're helping people all the time without even knowing. I had no idea, though. And then most recently, until quite, quite recently, he was the director of emergency management for New York City, helping almost 10 million New Yorkers, sometimes on their worst day. Zach, so proud to have you here. Thanks for having me.
00;02;37;02 - 00;02;52;15
Unknown
It's great to be with you. It's great to be with you. It's good to see you. So yeah, we'll talk about headstrong. I've never talked about it publicly, but it's I'm blown away by that. But yeah, we can get it. We'll get into it. But before that, why don't we get into, like, how you're sitting in this seat now?
00;02;52;16 - 00;03;11;20
Unknown
You went to Phillips Exeter, right? You went to Exeter. So for people who don't know, this is like one of the most storied preparatory schools in America, in the world. Then you went to Cornell, to Cornell. This is a pretty blue blood background to end up in the air for a Jewish kid in New York. Sure. Very blue blood.
00;03;11;21 - 00;03;31;20
Unknown
Yeah. Tell me about, like, the early days and how you decided to serve in the Marine Corps. Yeah. So I, by the way, you know my dad's marine, right? Once. Marina. Always a marine. Very proud in Brooklyn. Parris Island marine from Brooklyn, from Brooklyn, from Red hook. Wow, that's real Brooklyn. That's what he's. And especially when he was growing up, red hook was like, real Brooklyn.
00;03;31;21 - 00;03;49;25
Unknown
Oh, you know, it's like getting a little gentrified now, but it's like back then that was that was real. That was the docks. Exactly. Wow. So I, I grew up in a family where most of the most of the men in my family had served, you know, World War two. My dad was in the Air Force for a stint.
00;03;49;27 - 00;04;08;22
Unknown
And service was always something that was really important for my family. Then when I went to Cornell, I played lightweight football, which is a varsity sport, just for those of us that are not, you know, smaller in stature, but so what played lightweight football. And our football coach was a guy named Terry Collin. What's the what's the cutoff for lightweight.
00;04;08;22 - 00;04;28;20
Unknown
So when when it used to be 150, 150 pounds. When I played it was 165. I was the smallest starter at 164, but it is 165 pounds. Two days before game time, it's now 185 because they peg it to the size of the average American male. So as Americans have gotten larger, the lightweight has had the standard has changed.
00;04;28;22 - 00;04;49;12
Unknown
It's now 185 pounds. But the football coach there for years is named Harry Colin. And he was a marine officer, had served in Vietnam, badly wounded Silver Star. And he really encouraged me to join the Marines. And I sort of didn't know exactly what I wanted to do when I joined the Marine Corps. But my entire life, I've been a big, big fan of optionality.
00;04;49;12 - 00;05;07;12
Unknown
And I knew that if you go into the Marine Corps, unlike the other services, you sort of have to declare what you're going to do as you're going in in the Marine Corps as an officer, you get commissioned, you go to the basic school, and then based on your class ranking, you can pick whether you're going to flight school, infantry, logistics, drive a tank.
00;05;07;15 - 00;05;26;23
Unknown
You had tanks back then, artillery. So I knew that it would sort of give me some more optionality. And then speaking to Coach Cullen, you know, I really sort of fell in love with this idea that that the Marine Corps was really one of the top leadership laboratories in the world, and that it was a great place to leave school and learn a lot about leadership.
00;05;26;29 - 00;05;49;06
Unknown
Yeah, yeah. And so you commissioned right out of Cornell, commissioned right out of Cornell. I was commissioned August 11th, 2001 month later, nine over 11 happened. And I was actually I was in buds at the time. Were you in? Wow. So I was in buds. And where were you? In buds in Coronado. First phase of buds. So essentially like that's why I think in our lives, part of our friendship is based on the fact that our trajectories have been so parallel.
00;05;49;06 - 00;06;08;17
Unknown
So we were literally starting our military officer careers when nine over 11, right? When the crazy thing about that is when you think about when we were joining the guys that were our age were sort of at the tail end of Nam. Yeah, yeah. Now were those and our tactics reflected and our tactics reflected it. Yeah. No 100%.
00;06;08;17 - 00;06;32;02
Unknown
That was like that was what we were learning. Right. But it's also important like we we entered when it was a peacetime military and the sort of conception was peacetime military. You know, in some ways the Seal teams were a shoot dive jump club prior to nine over 11, right? Pejoratively. Oh, yeah. I thought the I thought the biggest thing I was going to do was IMU deployment, where maybe you evacuate an embassy and that you punch a card and you go home, right.
00;06;32;03 - 00;06;49;20
Unknown
And then and then, as you know, the world totally changed on September 11th. And so fast forward, ultimately you find yourself as a platoon commander in Iraq. Yeah. So I went in with a flight contract. I was supposed to go flight school, and when nine over 11 happened, I was worried that if I spent three years in flight school, I'd missed the war.
00;06;49;21 - 00;07;12;29
Unknown
So I dropped my flight contract, went infantry, and served one sort of deployment after the initial invasion, where we went ashore in Iraq for a short period of time as a mute appointment, and then volunteered for the next deploying unit, which was third Battalion, first Marines. And that was when we went into Fallujah in 2004. Yeah. And ultimately, I know this this shit doesn't matter.
00;07;12;29 - 00;07;29;00
Unknown
But you're in a Bronze Star for that, obviously. But that was like a serious combat deployment, right? That was a very serious combat deployment. And and I was. I'm incredibly proud to have been in three one during that time to have been a part of that. And, you know, in that in that unit, we are still very close today.
00;07;29;00 - 00;07;52;15
Unknown
In fact, when I was Commissioner Mercy Management, one of the guys in my detail who I was in the truck with every single day, a guy named John Saul was retired marine first sergeant, now NYPD. He and I were in three, one together 20 something years ago, you know, and it's like having a guy like that in the truck with you every day when you're dealing with the politics of City Hall or stuff around the city, you know, you got somebody you can really trust, you can talk to about anything and that you've really been there with.
00;07;52;16 - 00;08;14;14
Unknown
Yeah, yeah, I was with some of the boys last night, and truer words never spoken like it is hard to replicate that experience of serving with somebody overseas. Yeah. Okay. So you finish your you finish your time in Fallujah. How long did you stay post that second Iraq. So I was I was supposed to get out after that, and I was going to go to grad school.
00;08;14;14 - 00;08;33;09
Unknown
And the regimental Apso at the time was he's now retired, I think three star, two star named Sparky Wren. Fourth, he'd been the lightweight football coach at the Naval Academy, called me into his office as I was leaving, as we were getting ready to leave Iraq, and he said, I heard you're getting out. Really want you to stay in.
00;08;33;15 - 00;08;51;08
Unknown
I'll help you get any job you want in the Marine Corps. If you stay in. And I'm Jewish and there was a job to deploy to Israel as a UN observer for like six months, and I was like, if I can get that job and go to Israel and find my Jewish wife in Israel, I will sign the papers for two more years.
00;08;51;08 - 00;09;11;29
Unknown
So this is like classic. I know, by the way, that like, no battle plan survives the first shot. No no, no. Are you ready? Yeah. No. And by the way, I married an Irish Catholic girl from Boston. So like this. So I signed the papers for two more years. I leave Iraq, I go home on post-deployment leave, I come back, regimental wants to see.
00;09;12;01 - 00;09;27;16
Unknown
I go to his office. Colonel. He's colonel. Reinforced the time. Colonel. Fourth. How are you? Great. I got good news and bad news. What's the good news? You can have any job you want in the Marine Corps. I'm going to Israel. That's the bad news. We can't support that job anymore. I was like, why already signed up for two more years, sir.
00;09;27;17 - 00;09;52;18
Unknown
So I ended up getting detailed to a unit time called the Foreign Military Training Unit that then became the precursor to Marsac and helped. It was. It was a great experience because I helped build Marsac. I was helped build the recruiting, screening, assessment and selection pipeline. I was on one of the first teams to deploy, and it was it was an incredible experience of seeing and helping build, you know, a military unit from from the ground up.
00;09;52;19 - 00;10;09;18
Unknown
Yeah. And I don't know that we've actually talked about this, but I was intimately familiar with the genesis of Marsac because I was part of the so-called debt one or debt one out of one. With that, I can't remember his precursor, the precursor. Right. The colonel, the bald guy who was his name. He's a legend. Yeah. I'm legend.
00;10;09;18 - 00;10;31;18
Unknown
Get on his name. But he didn't he disappear in Africa for a little bit of. Yeah, yeah, he was probably running an African country right now. He's a wild guy. But anyway, so he deployed with us overseas at Seal Team one and stuff. So yeah those that's that's extraordinary. And like for people who don't know, you know, the inclusion of the Marine Corps into Special Operations Command is sort of a sort of tectonic shift in Marine Corps philosophy.
00;10;31;18 - 00;10;51;14
Unknown
And yeah, and some like amazing American warriors from Marsac now. Amazing. Okay. So then now you've signed up for two more years, you finally the Marine Corps really kind of gave it to you. Rico really gave it to me. You know, it's the. Yeah, the big green weenie, as they call it. But it was so glad I had that experience, you know, it was incredible.
00;10;51;14 - 00;11;17;11
Unknown
And I got to do some really interesting work in Africa, parts of the Middle East. One of the best times I had in, in the Marine Corps was my boss, Colonel Pete, who was one of the first guys helping stand up. He just sent me around Centcom to to to embed with special operations units and so grew my hair out, went bounced around a bunch of different countries, had a travel credit card and it was fantastic.
00;11;17;12 - 00;11;43;20
Unknown
It was fantastic. And I came back and, you know, just had to give a report to everybody about what the Marine Corps should build. And it was another one of those classic moments where I said, you know what? We really need no offense to Navy Seals. What we really need is guys that can go downrange, you know, eat the local food, speak the local language, you know, do foreign internal defense, unconventional warfare, sort of those like more classic, unconventional Green Beret type missions.
00;11;43;20 - 00;12;07;14
Unknown
And the Marine Corps was literally like the Heisman. It was like, that's great. Thanks. We're going to do more direct action and specialized reconnaissance. It was like, you know, like, that's awesome. But like, we're going to be door kickers. Yeah. And I was like, you know, yeah, yeah, I get it, I get it. That's really interesting. It's good foreshadowing for the rest of our conversation, because in essence, what you were doing was you were asked to do a startup within an existing organization.
00;12;07;16 - 00;12;33;24
Unknown
And part of our one of our themes here is that you don't always have to just like be Steve Jobs, building a computer in your garage and a product. Right. It's also possible to be entrepreneurial within organizations. And it sounds like you had a really good sort of beta experience in your last Marine Corps tour. Even even on my second deployment before going into Fallujah, I was in charge of one of the first successful Iraqi military units since I was building an Iraqi military unit in Iraq.
00;12;33;24 - 00;12;55;01
Unknown
And that, too, was very entrepreneurial. And I think that there are some real lessons from both of those experiences. And I think to your point, you know, I think you're right. A lot of times people think when they need to start a company, they need to go out and do it in their garage. And sometimes it makes a lot more sense to do it when you have some infrastructure and support around you, and it can take away some of the risk.
00;12;55;02 - 00;13;12;02
Unknown
Yeah, yeah. And I mean, the other thing is like especially like coming from the military, we often have this like I'm going to push all my chips in and go, right. But the truth is many startups are built like people have their 9 to 5 and they build their startups and they're 5 to 9. And that also is a de-risking mechanism.
00;13;12;03 - 00;13;37;29
Unknown
Right? So there's no like single set solution or single pathway. So what did you do immediately when you transitioned out of the service. So I did a bunch of stuff. I did some consulting work overseas. I did made a film, a documentary film about the war in Iraq and about Al Anbar. And then, you know, about two years after I'd been out, I started to see that we started losing more Marines to suicide than we had in common.
00;13;37;29 - 00;14;05;11
Unknown
And I was in one of the hardest hit battalions of the Iraq War. We lost 33 Marines in Fallujah. I think about 576 of our Marines and sailors were wounded in Fallujah. This is, you know, one of the hardest hit battalions. And we started seeing that, you know, losing some of our guys to suicide. And this is like in 2009, 2010, 2011, nobody wanted to talk about mental health, especially in the military.
00;14;05;17 - 00;14;29;29
Unknown
Nobody wanted to take this stuff seriously. There was huge lines at the VA and it was impossible to access care. And I sort of realized that the big problem was sort of. And so I was talking about this with with two very successful finance guys, guy named Al Rabal and a guy named Dave Petracca. And Al Rebel had been in therapy most of his life.
00;14;29;29 - 00;14;54;18
Unknown
And he is when I say successful, he's insanely successful. And he said, I don't understand why veterans can't get this type of care. I yet if I need to see the top psychiatrist in New York City tomorrow morning, I can do it. Regardless of whether they accept insurance or how busy they are, they'll fit me in. And that sort of became the foundation for, for, you know, answering the question, how do we build a program that can provide veterans with world class care that's easily accessible?
00;14;54;19 - 00;15;16;19
Unknown
No paperwork, no bureaucracy, and it's free. And I fortunately had some relationships at while Cornell Medical Center here in New York City with some amazing psychiatrists and therapists, woman named doctor, an beta clinician named Gerard. And so we started building this program here in New York City. And, you know, we our first year, we maybe treated like six people.
00;15;16;19 - 00;15;36;25
Unknown
And we just saw that there was magic there. People were getting better and that PTSD was something that people could recover from and especially if they got the right care. And so we started really growing that program. And now it's one of the largest mental health care providers in the US. We're treating thousands of veterans a month. Really, really proud of that team.
00;15;36;25 - 00;16;05;26
Unknown
But that was not something I ever sort of thought even imagine going into. Right when we were in the service, it was like, you go see the wizard, you know, if you got a mental health program, but it wasn't something that was taken seriously or the bartender or the bartender. Yeah, exactly. And I think our generation of vets, and I think the country has benefited from this because I think we have sort of normalized mental health care and been at the vanguard of that, that people are now willing to get help.
00;16;05;27 - 00;16;27;18
Unknown
Veterans are willing to get help. But I was that guy, right? Like, you know, knuckle dragging frogmen, you know, and I actually thought I had spoken for a long time about how, you know, I actually believed that I had post-traumatic growth from my military experiences, which is possible. Right? Like stress produces adaptation, and we grow from this, right, even when we're working out.
00;16;27;25 - 00;16;50;22
Unknown
And so for a long time and I built organizations devoted like I knew it was a problem. But my focus, the focus of my work, had been on veterans potential. Right. Team Rubicon mission continues. Right. Thinking of veterans as assets, not liabilities. And I honestly thought I was kind of immune to it. Right? I thought that I and I saw my our friends suffering around us, but I was like, you know, I got this.
00;16;50;23 - 00;17;05;18
Unknown
I'm good. And then I went to Ukraine and it all came flooding back to me, like the war in Ukraine. Somehow, all like our dead friends. Over the years, all the guys we had lost, it all came back and I didn't know what to do. And I was still, you know, I've been in and out of the reserves many times.
00;17;05;18 - 00;17;31;13
Unknown
And so, like, what did I do? Like I called headstrong because I'd love to hear that. And it was crazy. Right now, let's be clear. The VA has gone tremendously better. Right? But like there's still something there's still stigma, especially in the special operations community. And for me to be able to anonymously call up a provider and not think about who's going to pay for it or anything like that, zero friction as frictionless as possible.
00;17;31;16 - 00;17;55;12
Unknown
And it's fucking worked, man. So I am personally grateful. I love to hear that. It's it's amazing. It's amazing. And look, I'm totally clear. I have like 1% of like what other people have like a very small. But it's still it's like it's important, you know, like you go to the gym, you. And that's the other thing. It's like I think what a lot of folks don't is it's it's a totally normal reaction to combat.
00;17;55;14 - 00;18;16;05
Unknown
I mean, even right now, I've been in this job managing emergency for the city for four years. My phone has not stopped ringing for four years. Right. And I was going to start my new job on Monday, and I just left my old job on Wednesday. And I realized, like, I need some time to self-regulate. I need to just take some time to breathe because like when you're constantly in fight or flight, right?
00;18;16;07 - 00;18;38;08
Unknown
That is. And these words weren't even in our vocab. They weren't even a vocabulary when you and I were serving. Right. But it's like that is being in fight or flight is fantastic. When you're in combat, it's fantastic when you're operational and you need to fix problems and operate at that level. But I've also got four kids, I've got a wife, you know, I want to be present and you need to learn how to turn that off.
00;18;38;08 - 00;19;00;07
Unknown
And that sometimes takes help and that's totally fine. What I love about the headstrong story is not just because I personally benefited from it, but also it's an amazing roadmap blueprint for veteran entrepreneurship. Right? Because you essentially you saw this problem, you identified a problem, which is the beginning of building any business or philanthropic organization. You find a problem, right?
00;19;00;09 - 00;19;23;28
Unknown
And then you had like you foraged around for hypotheses like, hey, I think I can fix this. How? But here's the crazy part. Then you beta tested it, right? Six people in the first year. This is not a wildfire success like you are not curing mental health in America with your six patients in the beginning. But what you've started to find was what we would call like in the biz product market fit.
00;19;23;29 - 00;19;46;19
Unknown
Right. And then people started coming to it, and then you scaled and grew the organization like this is startup 101. And I think we're a lot of veterans get it wrong is they might do these steps. But I think we come from a culture where people don't want to fail. And I think you also have to recognize that there's going to be times when you fail, and that's totally fine, and sometimes an early failure that redirects you is totally fine.
00;19;46;20 - 00;20;05;15
Unknown
Yeah. Right. And and I do see there are a lot of veterans who get caught up in a nonstarter up. I was one of these folks or a company that has just never going to scale, never going to grow. But you are so freaking. Yeah, I'll find a way or make find a way and you're just jamming that square peg into a round hole and it's like, yeah.
00;20;05;16 - 00;20;22;18
Unknown
And I think the antidote to that. Right. Because like, one of the things we like to do here is like, you know, give people tools and techniques and tactics for, for avoiding those kind of common startup mistakes. Right. The antidote for that is data, right? You have to listen to the data and you have to listen to your customers.
00;20;22;18 - 00;20;39;20
Unknown
Right. And you have to take feedback. And you know, I like to say when I like mentor council start up folks like strong convictions loosely held. Right. I got this like strong idea. But then I'm like listening to the universe and it's telling me like, oh, this shit isn't working, or we want something else. And so then you can pivot, right?
00;20;39;21 - 00;20;58;24
Unknown
And those fast, those early, fast pivots are so much easier than like transforming an organization later in course. Correct. And you need to be able to build an organization where you have that level of trust and humility that you can hold those strong convictions, but people are still not afraid to challenge you, and you change your mind or you realize you're wrong, right?
00;20;58;25 - 00;21;17;21
Unknown
Like that is really there's a lot of we are wrong all the time. All the time. Good. And you also built some other organizations, right? You built task and purpose. And why did you do that? What was the what was. So I had started this job site called Higher Purpose at the time, and we had a blog that was affiliated with it.
00;21;17;21 - 00;21;38;27
Unknown
This was, I think, in like 2011, 2012, and I had two really amazing editors who were sort of running the blog named Brian Jones and a young woman named Lauren Katzenberg, who's not The New York Times. And I don't know if you remember the time, but there was there was all these awful sort of websites out there, like just the tip of the spear.
00;21;39;00 - 00;22;01;27
Unknown
Marines United not aware of this at all. I mean, so they were, you know, they were targeting women in service members looking, asking for like, photos of of women naked. And it was like really awful stuff and harassment and bullying. And nobody was sort of calling them out. And Brian Jones, who is a former marine officer from New York.
00;22;02;03 - 00;22;26;02
Unknown
Sorry, former enlisted marine, Afghanistan veteran, said to me, we need to do something about this. And I was like, Brian, this is a blog for a job site. What do you want to do about it? And he's like, well, nobody's saying anything, and this is wrong. And there's all these women service members that are being targeted. And I like when somebody comes to you and they say something's wrong, we have to do something about it.
00;22;26;03 - 00;22;48;00
Unknown
Like, you kind of have to. And I was like, this might be the end of the job site, but like, he's not wrong. Somebody needs to say something. And so we did a big exposé on this site, just the tip of the spear. Jay tots is what it was called. So sort of just like an independent journalism foray thing, but on the blog site for the job site.
00;22;48;01 - 00;23;20;19
Unknown
Right. And, and we realized that there was like a real gap in the marketplace for, for reporting that was really for the the men and women who were actually enlisted and doing the work and giving them a voice. And that became task and purpose. And, you know, we I sold it in 20 2020, I think maybe 2021. But I'm very proud of the team that we built there, the work that they've done, I mean, like media is especially like such an issue.
00;23;20;19 - 00;23;47;17
Unknown
Media is never going to be a groundbreaking business. But I think we did some really impactful work and told some really, really critically important stories. And that was sort of the first one. And so that that sort of came around out of an amazing I didn't I didn't know the origin story. That's, that's that's really fascinating. Amazing. And then ultimately you just finished this like giant job, which is its political appointee job or you have to run it is it's a political appointee job.
00;23;47;17 - 00;24;09;04
Unknown
All commissioners in the city are appointed by the mayor, Eric Adams. Yeah. And I had been you know, I during all this time, I'd been involved in a lot of emergencies. I was in Haiti after the earthquake. I did hurricane Sandy during Covid. I built one of the only successful Covid field hospitals in the country, and I ran unsuccessfully for comptroller here in the city in 2021.
00;24;09;06 - 00;24;34;17
Unknown
Got to meet Eric Adams during that that campaign a bit. And then when he was building his team, he asked if I'd serve as the emergency management commissioner. And so I've been in the role for four years, have dealt with all sorts of emergencies. I mean, everything from cyber incidents, shootings, all types of extreme weather, heat, cold, extreme rainfall and earthquake, you know, wildfire smoke from Canada.
00;24;34;19 - 00;25;00;04
Unknown
Didn't you guys have earthquakes? We had a little earthquake here in New York City. We have space weather, meteor over. I think it was like 4.0. Californian here took us to the core in New York City. We had a meteor, space weather, cyber incidents. We had the migrant crisis, which was was massive here in the city. I mean, that was probably the biggest thing we had to deal with.
00;25;00;04 - 00;25;22;25
Unknown
And, and then told me or Mamdani that I would I would stick around to help with the transition. And then my last day was, was Wednesday with the with the team. And it's it was incredible experience and really love working for the city and so and so. Now on to bigger and better things. Awesome. Congrats. We can't wait to see what you do next.
00;25;23;01 - 00;25;48;06
Unknown
What I'm curious about what I really want to like double click on, are some of the things from your early military experiences that you think helped you in these major ventures that you did, whether it was starting a nonprofit, starting like a for profit business, even though it was mission oriented, you know, or serving in this like really, really big role as emergency manager.
00;25;48;09 - 00;26;07;20
Unknown
What are the lessons that you drew from Iraq and the Marines that really helped you? So I think I was very, very lucky. I had a lot of great influences in the Marine Corps. I had an amazing platoon sergeant where we had probably one of the most ideal platoon commander, platoon sergeant relationships, a guy named Nick Fox, who still a very close friend to this day.
00;26;07;20 - 00;26;33;25
Unknown
I had some amazing battalion commanders and my commander, Colonel Colonel Buell at three one, were just incredible influences. And I think, you know, the common thread throughout my life is like, you know, I've almost always been in 25 years and some sort of leadership or management job. And I think one thing I would encourage veterans to really think about is we don't do such a good job in this country of building leaders and managers.
00;26;33;25 - 00;26;51;21
Unknown
And generally what I've seen in different industries is folks, often when they get promoted, once they can do the job really well as a manager because they're managing people who did what they just did when they get promoted the next time. Now they're managing people who they've never done those jobs. Yeah, it's like two derivative or something. Yeah.
00;26;51;22 - 00;27;25;05
Unknown
And it's it's and that's when you really have to learn on real lean on real leadership and management abilities. And so, you know, I mean it's it's like the basic blocking and tackling, you know, be inquisitive, be humble, make sure you're taking care of your people and that you care about them and that you're putting them. You're making sure they're working on problems that are really important, not wasting their time, that they're resourced appropriately, and you're setting them up for success that, you know, I'd say half my job as the emergency management commissioner was dealing with emergencies.
00;27;25;05 - 00;28;01;00
Unknown
The other half was dealing with City Hall and sort of fending off City Hall and protecting our agency from City Hall and making sure that your people know that they have a strong advocate. And I think that is sort of, you know, whatever you're doing, it's whether it was building headstrong, it's sort of, you know, I have no background in healthcare, but I knew how to find somebody like Doctor Beta and Girard at Loria who did, and make sure they had what they needed to be successful and to really listen to them, but then also to ask questions, to maybe challenge them a little bit and get them to think differently about what they're doing.
00;28;01;00 - 00;28;38;29
Unknown
So that because sometimes what the experts have always been doing is not necessarily going to solve the problem. Right. But having that learning how to sort of have that tension. And I think when you're a young platoon commander in the Marine Corps and you have zero experience, all you have is is, you know, six months of the basic school, ten, 12 weeks that infantry officer course and a college education, and now you're deploying with a unit and you've got a, you know, the old man of the platoon and staff Sergeant Fox, 28 or 30 years old, and he's got four deployments in his belt.
00;28;39;01 - 00;29;03;20
Unknown
Like, you've got to learn how to really listen to that platoon sergeant, but also how to ask the questions and lead and make sure that you're not just sort of leaning on experience, but bringing in innovation and and pushing things forward. And I think like, like learning how to operate in that space is is critical success in any endeavor as a leader.
00;29;03;23 - 00;29;24;27
Unknown
Agreed. How about dealing with setback and loss? I mean, look, in the civilian world, we don't have, thank God, most of the time, the equivalent of, like having people in your unit killed. Right. But we do have like, extraordinary setback and challenges and stuff. How do you deal with setback and loss? It's it can be really hard.
00;29;24;29 - 00;30;05;17
Unknown
And I think you have to remember and be gentle with yourself that it's all part of the process. And I think also like, look, I've now been in a job in the most intense media environment and one of the only local press that sort of still pay attention. Right. And everything that we do is under incredible scrutiny. And I remember when I ran for office, and I don't want to give any benefit to this internet troll, but like I said, something about, I think it was about I know exactly what it says about Rikers Island and that we still needed to have a solitary confinement to protect prisoners, protect guards.
00;30;05;20 - 00;30;26;05
Unknown
And there's this kid who just blasted me online, this DSA far left wing. And I just I couldn't sleep all night about this. And I'm now, like, thinking about it. I'm like. Like it didn't matter, right? Like. And what I've learned over the last four years is like, you just got to show up, do the work. The scrutiny doesn't matter.
00;30;26;07 - 00;30;58;24
Unknown
Setbacks, failure. It's all part of learning and developing and and you just got to grow from it. And I think if, if you're not willing to do that, you know, I mean that's just part of it. I mean, think about like when you're going through infantry training and you twist your ankle or, you know, I had friends that that broke a leg during a mortar hike and had to recycle through infantry officer course or, you know, you, you know, whatever it is, it's all part of your growth and development.
00;30;58;24 - 00;31;18;11
Unknown
And I think just building that resilience and it's like and learning to laugh about it. Right. Like it's like like learning. And my mom used to say, and my mom was one of the most amazing women ever. I lost for a couple of years ago. And she's still with me every day. And one of the things she would always say to me is just don't lose your sense of humor.
00;31;18;11 - 00;31;45;09
Unknown
And I think if you can learn to laugh through the setbacks and the loss and the difficulties, I mean, think about it. You go to a funeral and you tell stories about one of the guys you lost, right? And like, you have to find yourself laughing about these stories, right? It's like you're bringing joy to each other. And I think, like, that's part of it too, is like, is is reminding yourself that these things are are not as big of a deal as you might make them out to be.
00;31;45;10 - 00;32;05;23
Unknown
Yeah. I also think when I think about the veteran entrepreneurial landscape, I think that is one of our competitive advantages. There are lots of things that make it tough to be a better an entrepreneur like that sometimes. Never quit attitude when you should be finding a way around the obstacle instead of trying to run through the brick wall.
00;32;05;25 - 00;32;28;00
Unknown
But we have some competitive advantages. One is perspective, right? Because we've suffered real loss and and real consequences. Right? Oh, your company failed like big deal. Zach lost seven guys in Fallujah, right? Big fucking deal. Your company folded, right? So one is perspective and the other is humor, right? There is nobody funnier than, like. And we'll laugh about anything.
00;32;28;02 - 00;32;47;29
Unknown
Anything. And it's terrible. The darkest of dark. The darkest of dark. Yeah. When that angry B is flying over your head, you know, and like, your buddy is heckling you, right. Like that. So I think those are actually competitive advantages for better entrepreneurs. Awesome. Zach, we like to finish with a section that we call rapid fire. So it's like shooting steel, right?
00;32;48;00 - 00;33;17;14
Unknown
Sure. Just tell me what comes to mind and I'll keep my head below gunfire in above water. What's suit? Here we go. Locked and loaded. Best investment you ever made. So the best investment I ever made was was in a friend's children's entertainment company that I 50 x my return in like two years, but the and then the company eventually sort of went under afterwards.
00;33;17;14 - 00;33;36;29
Unknown
But I got out. But really the best investment I've ever made is just. And I think this is really this sounds like such a cliche, but it's it's the hamburger I bought my wife on our first date. It's the relationship I have with her and my and the children that I have. And it's the, the, the people that I've surrounded myself with.
00;33;36;29 - 00;34;04;06
Unknown
Because when you put yourself in and surround yourself with the right people, that foundation is the key to everything. Yeah. Shout out to Meredith. She's definitely way too cool for you. She is way too pretty. Way too cool. Way too smart. I mean, even I'm a first born Jewish son, which means something like in the pantheon of of of families like, you know, and my mom, who loved and adored me my entire life.
00;34;04;06 - 00;34;23;07
Unknown
But when I got together with Meredith, she was like, I don't know what she's doing with you. Yeah, I really don't know what she's doing with you. Yeah, well, your mom was a wise woman. She was a wise woman. Yeah. All right. Worst financial mistake you ever made. Oh, there's been a lot. I think probably one of the biggest ones is not signing up for the GI Bill initially when I was in the Marine Corps.
00;34;23;08 - 00;34;41;00
Unknown
Right. I'd already been to college. I didn't think I was going to need it. I actually did that, too. It was the old Montgomery before. It was the old Montgomery, for Paul came with the new and thank God they did the new GI Bill. But it was it was just such a dumb mistake. And yeah, I mean, take advantage of those things.
00;34;41;02 - 00;35;01;22
Unknown
Totally. Yeah, yeah. Well, we got that in common to military habit. You'll never lose a military habit. I'll never lose. It's definitely not the haircut because I had kettle black. I mean, I wake up insanely early. Yeah, I wake up insanely early. I like to get my workout done first thing in the morning. I have that habit as well.
00;35;01;22 - 00;35;15;28
Unknown
And I don't know if I would call it a habit or a curse, but yeah, yeah. It's both. I mean, even, you know, when I left this job, emergency management, the next morning, I thought I was going to sleep. Later, I was like 4 a.m., eyes wide open. It's like, I guess I'm going to the gym. There you go.
00;35;15;29 - 00;35;39;02
Unknown
Book. That changed your mindset. One of my favorite books is, oh, you should have sent this to me because there's there's a lot of great ones out there. Barbarian Days by William Finnegan, which is a great surfing book. And but it's about a guy who's a barbarian. He's traveling, world surfing. He lands in South Africa, gets involved in the anti-apartheid movement, and he becomes a citizen.
00;35;39;02 - 00;36;00;14
Unknown
And he sort of leaves his barbarian days behind. And I think that moment of finding real purpose was is incredibly meaningful, Zach, for people who want to follow along with what you're doing, what's the best way to connect or fall at the axis col? Everywhere. Everywhere. Yeah. LinkedIn. All the LinkedIn, Twitter, Instagram. Yeah. All those good places. Great, awesome.
00;36;00;14 - 00;36;24;05
Unknown
Well, thank you again, brother, and honored to have you to be with you. All right. Thanks for locking in with us today. Shout out to Siebert Valor and Siebert Financial for supporting our journey. We'll be back next week with another powerhouse conversation. More founders, more builders and leaders who are playing offense in life and in business. Make sure you're subscribed to our YouTube channel for exclusive content and extended cuts of your favorite episodes.
00;36;24;06 - 00;36;27;22
Unknown
Until next week. Stay tactical. Stay driven.